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Synlett 2016; 27(19): 2689-2694
DOI: 10.1055/s-0036-1588302
DOI: 10.1055/s-0036-1588302
letter
Organopromoted Direct Synthesis of 1,1-Diphenyl-3-arylindanes via Formal [3+2] Cycloadditions of Triphenylcarbenium Tetrafluoroborate with Styrenes
Further Information
Publication History
Received: 12 June 2016
Accepted after revision: 05 August 2016
Publication Date:
29 August 2016 (online)
Abstract
A formal [3+2] cycloaddition of triphenylcarbenium tetrafluoroborate with structurally different styrene derivatives has been developed. A combination of benzophenone and Et3N is key for promoting a formal [3+2] cycloaddition of triphenylcarbenium tetrafluoroborate with styrenes affording 1,1-diphenyl-3-arylindanes in moderate to good yields. The reaction mechanism of this transformation is also discussed.
Key words
styrenes - triphenylcarbenium tetrafluoroborate - indanes - formal [3+2] cycloaddition - organocatalystSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588302.
- Supporting Information
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References and Notes
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- 16 General Procedure for the Synthesis of 1,1,3-Triphenylindane (6a) A round-bottom flask equipped with a magnetic stirrer bar was charged with styrene (1.0 mmol), benzophene (0.3 mmol), Et3N (1.0 mmol), and toluene (2.5 mL). Triphenylcarbenium tetrafluoroborate (1.5 mmol) was then added, and the resulting mixture was allowed to react at 80 °C for 48 h. After the end of the reaction, the mixture was filtered through a plug of Celite® and eluted with hexane–EtOAc (8:2). The filtrate was concentrated in vacuo and purified by column chromatography on silica gel. The final product 6a was obtained in 77% yield as a white solid, mp 111.5–112.5 °C. Analytical TLC on silica gel: R ƒ = 0.40 (hexanes–EtOAc = 9.9:0.1). IR (KBr): νmax = 3080, 3061, and 3025 (aromatic), 2966, 2928, and 2862 (CH of aliphatic), 1596, and 1491 (aromatic), 1470, 1454, and 1444 (CH of aliphatic) cm–1. 1H NMR (300 MHz, CDCl3): δ = 7.35–7.16 (m, 17 H), 7.1 (d, J = 6.8 Hz, 1 H), 6.92 (d, J = 6.8 Hz, 1 H), 4.2 (dd, J = 6.4, 11.1 Hz, 1 H), 3.2 (dd. J = 6.4, 12.6 Hz, 1 H), 2.90 (dd, 11.1, 12.6 Hz, 1 H). 13C NMR (75 MHz, CDCl3): δ = 149.41 (C), 148.05 (C), 146.66, (C), 145.83 (C), 143.88 (C), 128.61 (3 CH), 128.54 (3 CH), 128.52 (2 CH), 128.03 (2 CH), 127.99 (2 CH), 127.19 (CH), 126.72 (CH), 126.62 (CH), 126.28 (CH), 126.08 (CH), 126.04 (CH), 125.03 (CH), 60.84 (C), 54.13 (CH2), 49.01 (CH). HRMS (ESI-TOF): m/z [M + Na]+ calcd for C27H22Na: 369.1619; found: 369.1531.